This sorta happened to me once too. In the B/CS area. White dude with no teeth.

Him and his crew came and mowed our lawn for $50 or something. They knocked on our door.

He came back two weeks later asking if I could lend him $20 and a ride to the bank to cash a check. We did exactly that. He said he would come back and mow my lawn at another time. He actually did. I wasn't expecting the money back honestly.

He came back another time saying his van had broken down and some lady had given him a ride and asked if I could lend him $20 again and would come back and mow the lawn. He was good for it the first time so I gave it to him. Never saw him again.

Wasn't nearly as sketchy as your dude though. And was true to his word the first time.

Funny thing is he came back like maybe 10-12 months later but this time my roommate answered it and said it was that same dude. Gave him no help this time. Obviously he hadn't changed his stupid ass ways of life.

I didn't tell my roommate that I lent the guy $20 though. Didnt want to look like a fool.